抗局所麻酔薬の化学的及び薬理学的研究 (第2報)
p-Aminobenzenesulfonyl-diethylaminoethanolの合成
1953 年 73 巻 5 号 p. 478-480
詳細
1953 年 73 巻 5 号 p. 478-480
p-Aminobenzenesulfonyl diethylaminoethanol (I), m.p. 105°, an antagonist of procaine, was obtained by hydrolysis with hydrochloric acid of p-acetaminobenzenesulfonyl diethylaminoethanol, m.p. 77°, formed by the condensation of p-acetaminobenzenesulfonyl chloride, m.p. 149°, and diethylaminoethanol, b.p. 160-161°. (I) is extremely stable in acids and alkalis but when heated with conc. hydrochloric acid in a sealed tube for 1 hour at 140°, it decomposes into the two components, sulfanilic acid and diethylaminoethyl chloride hydrochloride, m.p. 202-204°. (I) cannot be obtained when diethylamine and p-acetaminobenzenesulfonyl chloroethanol, m.p. 138°, are heated in a sealed tube for 10 minutes at 130°, only giving the sulfanilate, m.p. 187-188°, of 3-diethylaminoethyl chloride, assumed to have been formed by the intramolecular rearrangement followed by decomposition of p-acetaminobenzenesulfonyl diethylaminoethanol hydrochloride.
